Transition-metal-catalyzed asymmetric C–H functionalization has gradually emerged as a powerful tool for the creation of structural and chiral complexity in an atom-and step-economical fashion.The nature of this stra...Transition-metal-catalyzed asymmetric C–H functionalization has gradually emerged as a powerful tool for the creation of structural and chiral complexity in an atom-and step-economical fashion.The nature of this strategy provides a variety of methodologies to overcome the limitation of enantioselective desym-metrization caused by the synthesis of preformed multifunctional symmetric substrates.展开更多
To prepare chiral monomer with single chiral center and higher stereospecificity, a pair of amino-functionalized chiral 3,4-propylenedioxythiophene(ProDOT) derivatives, chiral(3,4-dihydro-2 H-thieno[3,4-b][1,4]dioxepi...To prepare chiral monomer with single chiral center and higher stereospecificity, a pair of amino-functionalized chiral 3,4-propylenedioxythiophene(ProDOT) derivatives, chiral(3,4-dihydro-2 H-thieno[3,4-b][1,4]dioxepin-3-yl)methyl 2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate(ProDOT-Boc-Phe), were synthesized. Chiral poly[(3,4-dihydro-2 H-thieno[3,4-b][1,4]dioxepin-3-yl)methyl2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate](PProDOT-Boc-Phe) modified electrodes were synthesized via potentiostatic polymerization of chiral ProDOT-Boc-Phe. Chiral PProDOT-Boc-Phe films displayed good reversible redox activities. The enantioselective recognition between chiral PProDOT-Boc-Phe modified glassy carbon electrodes and DOPA enantiomers was achieved by different electrochemical technologies, including cyclic voltammetry(CV), square wave voltammetry(SWV), and differential pulse voltammetry(DPV).(D)-PProDOT-Boc-Phe and(L)-PProDOT-Boc-Phe showed higher peak current responses toward L-DOPA and DDOPA, respectively.展开更多
基金Financial support from the NSFC(21925109,21772170,21801223,and 21772179)the China Postdoctoral Science Foundation(No.2020M671689)the Center of Chemistry for Frontier Technologies of Zhejiang University is gratefully acknowledged.
文摘Transition-metal-catalyzed asymmetric C–H functionalization has gradually emerged as a powerful tool for the creation of structural and chiral complexity in an atom-and step-economical fashion.The nature of this strategy provides a variety of methodologies to overcome the limitation of enantioselective desym-metrization caused by the synthesis of preformed multifunctional symmetric substrates.
基金the National Natural Science Foundation of China(Nos.51762020 and 51603095)the Natural Science Foundation of Jiangxi Province(Nos.20171ACB20026 and20181BAB206015)+4 种基金the Jiangxi Provincial Department of Education(No.GJJ170662)the Innovation Driven"5511"the Natural Science Foundation of Jiangxi Province(No.20165BCB18016)Students Innovation and Entrepreneurship Training Program(No.20181204066)Projects for Postgraduate Innovation in Jiangxi(No.YC2017-X19)the Jiangxi Provincial Key Laboratory of Drug Design and Evaluation(No.20171BCD40015)for their financial support of this work
文摘To prepare chiral monomer with single chiral center and higher stereospecificity, a pair of amino-functionalized chiral 3,4-propylenedioxythiophene(ProDOT) derivatives, chiral(3,4-dihydro-2 H-thieno[3,4-b][1,4]dioxepin-3-yl)methyl 2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate(ProDOT-Boc-Phe), were synthesized. Chiral poly[(3,4-dihydro-2 H-thieno[3,4-b][1,4]dioxepin-3-yl)methyl2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoate](PProDOT-Boc-Phe) modified electrodes were synthesized via potentiostatic polymerization of chiral ProDOT-Boc-Phe. Chiral PProDOT-Boc-Phe films displayed good reversible redox activities. The enantioselective recognition between chiral PProDOT-Boc-Phe modified glassy carbon electrodes and DOPA enantiomers was achieved by different electrochemical technologies, including cyclic voltammetry(CV), square wave voltammetry(SWV), and differential pulse voltammetry(DPV).(D)-PProDOT-Boc-Phe and(L)-PProDOT-Boc-Phe showed higher peak current responses toward L-DOPA and DDOPA, respectively.
